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PROBLEM 7.42

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Organic Chemistry
Found in: Page 290

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Short Answer

Question: Give the IUPAC name for each compound.

a.

b.

c,

d.

e.

f.

Answer

The IUPAC name of the given compounds are as follows:

a. 1-fluoro-3,3,4-trimethylpentane

b. 3-ethyl-1-iodo-2-methylhexane

c. 1,3-dichloro-5,5-dimethylhexane

d. 1-bromo-3-iodocyclopentane

e. 2-chloro-6,6-dimethyl-octane

f. (2R)-2-iodo-4,4-dimethylhexane

See the step by step solution

Step by Step Solution

IUPAC naming

The organic compounds are named according to the specific rules that the IUPAC derives. The naming done through IUPAC are universally acceptable.

The first step is finding the chain that carries the maximal count of carbon atoms, substituent, and functional groups.

Numbering the carbon chain

  1. The numbering will take place from the carbon that carries a functional group.
  2. The prefix will be added according to the number of carbon chains; example: For one, two, three, and four carbons chains, “meth,” “eth,” “prop,” and “but” are used, respectively.
  3. If the carbon is saturated, “ane” is used as a suffix. If double and triple bonds are present, then “ene” and “yne” are used, respectively.
  4. Also, in the case of cyclo compounds, “cyclo” is used before the prefix.
  5. All the substituents are named in alphabetical order.
  6. If the compound is chiral, its configuration should be mentioned in the IUPAC name.

Explanation

a.The parent chain is of five carbons, so “pent” is used as a prefix. Also, the chain is saturated. Therefore, “ane” will be used as a suffix. Fluorine and three methyl groups are present at the first, third, and fourth positions, respectively.

Numbering of carbon chain in (a)

Hence, the final IUPAC name of the compound is 1-fluoro-3,3,4-trimethylpentane.

b. In the given compound, the longest chain is of six carbon atoms, so “hex” will be used as a prefix. At first, second, and third positions, iodine, methyl, and ethyl group are present, respectively.

The compound is saturated, so “ane” will be used as a suffix.

Numbering of carbon chain in (b)

Hence, the final IUPAC name of the compound is 3-ethyl-1-iodo-2-methylhexane.

c. The parent chain carries six carbon atoms, so the prefix will be “hex.” The first and third carbon include a chlorine atom, and the fifth carbon contains two methyl groups. The suffix “ane” will be used as the compound is saturated.

Numbering of carbon chain in (c)

Hence, the final IUPAC name of the compound is 1,3-dichloro-5,5-dimethylhexane.

d. The given compound is a cyclic compound. The ring contains five carbon atoms. Hence, “pent” will be used as a prefix. The compound is saturated. So, “ane” will be used as a suffix.

The numbering will be done according to alphabetical order. The numbering will be done from the bromine carbon atom. The iodine will get the third position.

Numbering of carbon chain in (d)

Hence, the final IUPAC name of the compound is 1-bromo-3-iodocyclopentane.

e. The parent chain is of eight carbon atoms. So, the prefix “oct” will be used. The suffix will “ane” is used as the compound is saturated. At the 6th position, a methyl group is used. The second carbon contains a chlorine atom.

Numbering of carbon chain in (e)

Hence, the final IUPAC name of the compound is 2-chloro-6,6-dimethyl-octane.

f. The parent chain is of 6 carbon atoms. Hence, “hex” will be used as a prefix. Due to saturated compound, the suffix will be “ane”. At second carbon, iodine is present, and at fourth carbon, two methyl groups are present.

The compound is chiral with the configuration “R” at the second position. The configuration should be mentioned while writing the IUPAC name.

Numbering of carbon chain in (f)

Hence, the final IUPAC name of the compound is (2R)-2-iodo-4,4-dimethylhexane.

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